Martha's Vineyard Rental Homes For Large Groups

Find a wonderful variety of Martha’s Vineyard vacation rentals for large groups and families. Find homes for large groups in Chilmark, Oak Bluffs, Edgartown, and other popular communities on Martha’s Vineyard. Whether you are looking for waterfront views, walking distance to the beach or close to downtown, find your perfect Martha’s Vineyard vacation home here! Scroll to view Martha's Vineyard vacation rentals below.

Martha's Vineyard Vacation Rentals for Large Groups

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Oak Bluffs, MA

Rental Price$7,000 to $14,500

Rental ID 126030

  • RTR Vacation Rental
  • Lease $7,000 to $14,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 5

The Weku House is a luxury, 5,000 square foot home located in the beautiful town of Oak Bluffs on Martha’s Vineyard. Originally built in the year 2000, this home was fully renovated in 2015. Elegantly decorated with designer furnishings and interior appointments, the meticulous attention-to-detail makes this home a unique vacation retreat. With a total of 5 bedrooms and 5 1/2 baths, the home features sleeping accommodations that include two master king suites with ensuite bathrooms, a bedroom with two twin beds, and another spacious queen-sized guest bedroom. Additionally featured is an attached 720 square foot private apartment. "The Apartment" at Weku House features a fully equipped kitchen with Bosch appliances, a queen-sized bedroom, private bathroom, in-unit washer and dryer and an open living and dining room. There is also a private deck with bistro seating. A most popular feature of the home is the spectacularly finished basement, which includes state-of-the-art entertainment come rain-or-shine. Features include: a fitness room, a Play Zone with PlayStation 4, and Wii gaming consoles, a 40 inch 4K high-definition TV and a multitude of board games. Also in the basement is a stunning custom designed bar area with icemaker, dishwasher, microwave and a Hi Def TV overlooking a customized pool table. A home theater with a 70 inch 4K high definition TV and surround sound complete this entertainment space. Add to all of this a 1.3-acre setting, a serene front porch with rocking chairs overlooking beautifully landscaped grounds and a rear deck with dining and seating areas surrounding a rectangular gas fire table, and a gas-powered outdoor grill. With great pride, we welcome you to The Weku House.

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Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Chilmark, MA

Rental Price$2,500 to $6,000

Rental ID 119742

  • RTR Vacation Rental
  • Lease $2,500 to $6,000
  • Village Chilmark
  • Bedrooms 4
  • Bathrooms 2

Located on the North side of Chilmark, this contemporary getaway offers a wide open living space with vaulted ceilings, stylish furnishings, a spacious deck and a stunning widow’s watch with water views. Completely renovated in 2012, this home feels like new and features a brand new kitchen with top of the line appliances, luxury showers with multiple fixtures and central air conditioning. Set on over two acres of land, the property boasts multiple gardens, a private outdoor shower and a fire pit. There are several Land Bank properties within walking distance, including the historic hiking trails at Waskosim’s Rock Reservation. For beach goers, you get access to gorgeous Lucy Vincent beach and are a bike ride away from the beach at Great Rock Bight, a well-kept secret among locals. The Chilmark Flea is just around the corner for those looking for an authentic up island experience. Perfect for families, this is a great venue to recharge and reconnect amidst some of the island’s most beautiful scenery.

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$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Vineyard Haven, MA

Rental Price$1,750 to $4,000

Rental ID 142176

  • RTR Vacation Rental
  • Lease $1,750 to $4,000
  • Village Vineyard Haven
  • Bedrooms 4
  • Bathrooms 3

Cheerful four bedroom, 3 bath home in a charming neighborhood just a mile from the village. Recently refinished there is an open kitchen, living, and dining area with sliders opening to rear deck. Walk to saltwater access or drive to public beaches.

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$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Oak Bluffs, MA

Rental Price$5,250 to $15,750

Rental ID 141578

  • RTR Vacation Rental
  • Lease $5,250 to $15,750
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 3

Endless views of the ocean, directly across from the water, and steps away from a sandy beach excellent for swimming. Gorgeously remodeled last summer (2018) and designed with a sophisticated California-meets-MV feel inside, our welcoming, centrally-air-conditioned, 4 bedroom house sleeps 10 and is a rarity in this area. Blonde wood wide plank flooring, new kitchen, new doors & windows, mattresses, and appliances including dishwasher, gas range, French door refrigerator with ice maker and a king size bed in a larger than usual (for OB) master BR. The house is airy and uncluttered, with a wide 3-sided wraparound porch, perfect for watching the annual fireworks, dining outside or watching the world go by. 4 well appointed bedrooms -- one downstairs and three upstairs (including a larger bedroom with a queen & 2 twins which is perfect for sharing). Second-story deck off the master bedroom offers views of the ocean, as well as Farm Pond. A second porch off the second & third upstairs bedrooms also has ocean views. Two sets of French doors from the kitchen and dining area open out to a larger portion of the deck and stunning ocean views. Updated bathrooms (glass-door subway tile walk-in shower downstairs, a deep soaking tub upstairs), wide porches to relax and dine on, and an open and connected feeling downstairs (a wood topped bar/island connects guests to the dining area and the kitchen, open french doors connect it all to the deck and the outdoor seating/dining). The house is set back from the road by a generous lawn, and is a very short distance (a few houses) to the bike path that runs along the island s edge & State Beach and into Edgartown, and within easy walking distance of both the Oak Bluffs ferry docking and the shops and restaurants in town and along the harbor, so you ll never have to search for a parking space to dine in-town in the high season. There s a large dining table inside & barbecue and additional outdoor seating/dining table on the porch, TV (televisions in the living room and the master BR). 1 king bed, 2 queen beds, 1 full sized bed, and 2 twin beds. Additionally, upon request/discussion, there is a back guest cottage aka "The Nest". The Nest has a good size upstairs bedroom (offering what is then a 5th BR); queen bed and a twin bed (sharing the same room), a deck off the bedroom that has water views (ocean and Farm Pond), The guest house is air conditioned with mini split.

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$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Vineyard Haven, MA

Rental Price$3,500 to $11,000

Rental ID 140361

  • RTR Vacation Rental
  • Property Name Harbor front home
  • Lease $3,500 to $11,000
  • Village Vineyard Haven
  • Bedrooms 5

Perched high on a sunny bluff, this quintessential Vineyard Haven harbor front home is located on “little Hatch Road” – that sweet little enclave lying midway between West Chop and downtown. Enjoy sweeping views of Vineyard Sound, East Chop and Cape Cod from your spacious, enclosed, heated porch or from the back lawn. From the lawn, mosey down the steps to your 146-foot private beach. The classic house is fully restored, yet preserves much of its vintage charm – buttery hardwood floors, soapstone kitchen sink, paneled butler’s pantry, Old World bathroom fixtures and more. With five bedrooms, two full baths there’s plenty of room for family and friends to spread out and enjoy.

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$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Oak Bluffs, MA

Rental Price$6,000 to $14,000

Rental ID 139055

  • RTR Vacation Rental
  • Lease $6,000 to $14,000
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 4

Luxury home located in a parkland setting in Sengekontacket - peaceful and serene yet close to downtown Oak Bluffs and the rest of the Vineyard. This new construction home has a large gourmet kitchen and wide open space adjacent dining and living areas. It is perfect layout for families to gather and socialize. The first floor opens onto a stone patio and grassy landscaped yard - ideal for grilling and outdoor entertaining. There is a large en-suite master bedroom on the first floor. Sliding doors open to a private back deck - perfect for enjoying your morning coffee. Four additional bedrooms are located on the second floor. Queen sized bedroom with private bath. Full sized bedroom with private bath. Two bedrooms with two twin beds give your family multiple sleeping arrangements. There is an association boat launch that is available for your kayaks.

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%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Vineyard Haven, MA

Rental Price$3,000 to $6,500

Rental ID 136744

  • RTR Vacation Rental
  • Lease $3,000 to $6,500
  • Village Vineyard Haven
  • Bedrooms 4
  • Bathrooms 2

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

Oak Bluffs, MA

Rental Price$3,000 to $7,000

Rental ID 136204

  • RTR Vacation Rental
  • Lease $3,000 to $7,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2

Beautiful home in a perfect location in Oak Bluffs. Fully renovated in 2015 including central A/C and huge deck with pergola! This home is very well kept and lovingly furnished for both style and comfort with a spacious layout for vacations with families and friends. Large two-story, classic Cape Cod style home with 4 Bedrooms and 2 Full Baths, includes large deck, screened porch, outdoor stone patio and furnished basement. Located close enough to the action of Curcuit Avenue in downtown Oak Bluffs, yet tucked away in a quit neighborhood, with easy access to key routes along County and Barnes Roads, this home is secluded by the surrounding forests of the school yards and Trade Winds Field and Trails. The expansive first floor includes a newly remodeled, open-concept kitchen, which opens up to a large great room with dining room and sitting areas and a separate family room with 55 TV. French doors and sliders open up to several, large outdoor areas, including a deck, a screened porch and a stone patio. The doors also allow wonderful island breezes throughout the home. A private bedroom is also located on the first floor, along with a renovated full bathroom. Oak hardwood floors are featured throughout the entire interior of the home. The second floor has 3 bedrooms and a full bath. The basement is furnished as a game room and home theater with a 65 TV and real 10 shuffle board table, as well as DVDs, games, cards and more. Families with children can also enjoy the benefits of Oak Bluffs school playground and tennis courts located adjacent to the property as well. The many beautiful outdoor spaces of the home seem endless. They include a large deck covered with cedar pergola and outdoor dining

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$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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West Tisbury, MA

Rental Price$1,500 to $4,000

Rental ID 135192

  • RTR Vacation Rental
  • Lease $1,500 to $4,000
  • Village West Tisbury
  • Bedrooms 4
  • Bathrooms 2

Live the sea-faring charm of Martha s Vineyard in this appealing, historic Sea Captain s home. Centrally located in West Tisbury village, this country farmhouse was home to members of the White House Staff when President Clinton made MV his "summer white house". The home features an elegant curved staircase in foyer and a "secret" back staircase leading from the kitchen to the master suite. There are 3-4 spacious bedrooms with air conditioners, desks, and sitting areas. There is a grand piano for your enjoyment. The living room has digital cable TV. Adjoining the living room is a separate dining room with a special farm "tavern" table constructed from a ship s starboard hatch cover, and charming country kitchen. Out of doors relax with a drink on the appealing front porch and watch the world go by. There is private rear patio and a charcoal grill. Walk to Alley s General store, café and deli - and you are steps away from the Famous Vineyard Farmers Market. The Sea Captain s home is located near two of most exquisite and unspoiled beaches. Relax at Lambert s Cove Beach or Long Point South Beach.

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Vineyard Haven, MA

Rental Price$2,150 to $4,000

Rental ID 135092

  • RTR Vacation Rental
  • Lease $2,150 to $4,000
  • Village Vineyard Haven
  • Bedrooms 4
  • Bathrooms 3

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details